This invention relates to perfluoralkylthioglycosides and their use as surfactants in biochemistry and in general surfactant applications.
Alkyl glycosides are well known and have long been used for biochemical research. However, they are expensive detergents and their use has been limited to small scale experiments.
Alkyl thioglycosides are disclosed in JP 61/7288(1986). These compounds possess much improved properties over the O-analogs and have many of the desirable properties usually required for solubilization, purification and reconstitution of membrane proteins. These properties include a high solubilizing power, non-denaturation of proteins, a high Critical Micelle Concentration (CMC), a non-ionic nature, optical transparency, high chemical purity, high solubility in water, stability to acidic and enzymatic hydrolysis, inertness to protein assays, and ease of synthesis.
A limited number of perfluoroalkyl glycosides have been reported, namely 1,1,1-trifluoroethyl glucoside, in Biochem. 9,(140) 2890-6(1970), and several 2-(F-hexyl)-ethanol and 11-(F-hexyl)-10-undecanol derivatives, namely 2'-F-hexyl)-ethyl substituted D-glucopyranoside, D-galacto-pyranoside, and 11'-(F-hexyl)-10'-undecenyl-D-maltoside, in Tet. Letters 29,(18) 2193-4(1988), and oligomeric glycosides derived from 1,1,11-trihydroperfluoroundecanol, in U.S. Pat. No. 3,598,865. No. perfluoroalkyl-thiosaccharides have previously been disclosed.